Stannous Chloride → HCID 131732284, compound

HRID 1424824Notes

Reaction equation

HRID 1424824 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[C:33]([F:35])[C:32]([N+:36]([O-])=O)=[C:31]([F:39])[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[Sn](Cl)Cl>CCOC(C)=O.C(O)C.O>[NH2:36][C:32]1[C:31]([F:39])=[CH:30][C:29]([N:24]([C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:23][C:8]3[C:9]([C:19]([NH:21][CH3:22])=[O:20])=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[O:11][C:7]=3[CH:6]=2)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:34][C:33]=1[F:35]

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 131732283HCID 131732283, compound

Product 1

HCID 131732284HCID 131732284, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5-cyclopropyl-6-(N-(3,5-difluoro-4-nitrophenyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (0.65 g, 1.16 mmol) and tin (II) chloride (0.66 g, 3.49 mmol) in EtOAc (10 mL) and ethanol (10 mL) was heated under reflux for 2 h. The reaction mixture was diluted with EtOAc and water and the suspension was filtered through celite. The organic layer was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-50% EtOAc/hexanes) to afford the title compound (0.34 g, 55%) as a white solid. LCMS (m/z, ES+)=530.2 (M+H+).

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationthe suspension was filtered through celite
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b03580c35b1540ba813e625cd91b0183
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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